EP0123719A2 - Verfahren zur Herstellung von 5-Acyloxymethyl-oxazolidin-2-on-derivaten. - Google Patents
Verfahren zur Herstellung von 5-Acyloxymethyl-oxazolidin-2-on-derivaten. Download PDFInfo
- Publication number
- EP0123719A2 EP0123719A2 EP83107961A EP83107961A EP0123719A2 EP 0123719 A2 EP0123719 A2 EP 0123719A2 EP 83107961 A EP83107961 A EP 83107961A EP 83107961 A EP83107961 A EP 83107961A EP 0123719 A2 EP0123719 A2 EP 0123719A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- compound
- alkyl group
- formula
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 44
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 36
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 239000012442 inert solvent Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- -1 lithium halide Chemical class 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 150000007514 bases Chemical class 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 239000007858 starting material Substances 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000004817 gas chromatography Methods 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000006188 syrup Substances 0.000 description 7
- 235000020357 syrup Nutrition 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 0 C*(OC(C*)CNC)=O Chemical compound C*(OC(C*)CNC)=O 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 235000008504 concentrate Nutrition 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- HAQRVJXVMSWGQK-UHFFFAOYSA-N 3-tert-butyl-5-(chloromethyl)-1,3-oxazolidin-2-one Chemical compound CC(C)(C)N1CC(CCl)OC1=O HAQRVJXVMSWGQK-UHFFFAOYSA-N 0.000 description 2
- SSMIUHOOMMVZNL-UHFFFAOYSA-N 3-tert-butyl-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound CC(C)(C)N1CC(CO)OC1=O SSMIUHOOMMVZNL-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- MGOLNIXAPIAKFM-UHFFFAOYSA-N 2-isocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=O MGOLNIXAPIAKFM-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- JKXONPYJVWEAEL-UHFFFAOYSA-N oxiran-2-ylmethyl acetate Chemical compound CC(=O)OCC1CO1 JKXONPYJVWEAEL-UHFFFAOYSA-N 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 125000004436 sodium atom Chemical group 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
Definitions
- the present invention relates to novel 5-acyloxymethyloxazolidin-2-one derivatives being a useful starting material for producing drugs, and processes for preparing the same. More particularly, the present invention relates to novel 5-acyloxymethy- oxazolidin-2-one derivatives having the formula (I): wherein R 1 is an alkyl group; R 2 is an alkyl group, an aryl group or an aralkyl group, and processes for preparing the same.
- the compound (I) of the present invention is a novel compound unknown in any literature and important as a starting material for producing drugs. Particularly, the compound (I) is expected to be industrially available as an important starting material for a new optical resolution process of preparing optically active ⁇ -adrenergic receptor blocking agents.
- 5-acyloxymethyloxazolidin-2-one derivatives having the formula (I): wherein R1 is an alkyl group; R 2 is an alkyl group, an aryl group or an aralkyl group.
- the present invention also provides processes for preparing the 5-acyloxymethyloxazolidin-2-one derivatives having the formula (I).
- Fig. 1 is a NMR spectrum chart of the compound (I) of the present invention obtained in Example 1.
- the substituent group defined as R 1 in the formula (I) includes an alkyl group, e.g. an alkyl group having 1 to 6 carbon atoms, preferably t-butyl group or isopropyl group.
- the substituent group defined as R 2 in the formula (I) includes an alkyl group, e.g. an alkyl group having 1 to 17 carbon atoms; an aryl group, e.g. phenyl group or a substituted phenyl group such as p-chlorophenyl group or p-hydroxyphenyl group; or an aralkyl group, e.g. benzyl group.
- the compound (I) of the present invention is prepared by the following four methods.
- the compound (I) is prepared by reacting a compound having the formula (II): wherein R 1 is as defined above, X is a halogen atom, and a compound having the formula (III): wherein R 2 is as defined above, M is an alkali metal atom or NH 4 + , in an inert solvent.
- the substituent group defined as R in the formula (II) is an alkyl group, e.g. an alkyl group having 1 to 6 carbon atoms, preferably t - butyl group or isopropyl group, and the substituent group defined as X in the formula (II) is a halogen atom, e.g. chlorine or bromine atom.
- the substituent group defined as R 2 in the formula (III) is an alkyl group, e.g. an alkyl group having 1 to 17 carbon atoms, an aryl group, e.g.
- the substituent group defined as M in the formula (III) is an alkali metal atom, e.g. sodium atom or potassium atom, or NH 4 + .
- the compound (III) is employed in an amount of not less than 1.0 mole, generally 1.05 to 1.5 moles, per 1 mole of the compound (II).
- the inert solvent are, for instance, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, and the like. Since the reaction is heterogeneously proceeded depending on the kind of the solvent, it is preferred to carry out the reaction with sufficiently stirring.
- reaction can be carried out at a temperature of from 50°C to the reflux temperature of the inert solvent, it is preferred to carry out the reaction with refluxing for reducing the reaction time.
- the reaction is usually completed in from 1 to 24 hours.
- phase transfer catalyst e.g. benzyltriethylammonium chloride or Crown ether such as 15-Crown-5.
- the reaction mixture is once cooled, the insoluble material in the mixture is filtered off, and then the filtrate is concentrated under a reduced pressure.
- an organic solvent such as ethyl acetate or hexane, and the mixture is repeatedly washed from one to three times with water or sodium bicarbonate. After dehydrating and drying the organic layer, the desired compound (I) is obtained by concentration. Furthermore, the obtained compound (I) is purified by means of column chromatography on silica gel to give the pure compound (I).
- the comound (I) is prepared by reacting a compound having the formula (II): wherein R 1 and X are as defined above, a compound having the formula (IV): wherein R 2 is as defined above, and a compound having the formula (V): wherein M is as defined above, in an inert solvent.
- the compound (IV) and (V) are employed, respectively, in an amount of 1.0 to 1.5 moles and 0.5 to 1.2 moles, per 1 mole of the compound (II).
- the solvent are, for instance, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, and the like. Since the reaction is heterogeneously proceeded depending on the kind of the solvent, it is preferred to carry out the reaction with sufficiently stirring. Though the reaction can be carried out at a temperature of from 50 C to the reflux temperature of the inert solvent, it is preferred to carry out the reaction with refluxing in order to shorten the reaction time. The reaction is generally completed in from 1 to 24 hours. After completing the reaction, the reaction mixture is purified by the same manner as in the first method to give the desired compound (I).
- the comound (I) is prepared by reacting a compound having the formula (VI): wherein R 1 is as defined above, and a compound having the formula (VII ⁇ : wherein R 2 is as defined above, in the presence of a catalyst.
- the substituent groups defined as R 1 and R 2 are the same as those described in the first method, respectively.
- the use of equimolar amounts of the compound (VI) and the compound (VII) is sufficient.
- the reaction can be proceeded with or without using a reaction solvent, examples of the solvent are, for instance, benzene, toluene, N,N-dimethylformamide, acetonitrile, and the like.
- lithium halide is effective, e.g. lithium chloride or lithium bromide is generally used.
- the reaction can be carried out at a temperature of from 50°C to the reflux temperature of the inert solvent, it is preferred to carry out the reaction with refluxing in order to shorten in the reaction time.
- the reaction is completed in from 3 to 48 hours. After completing the reaction, the reaction mixture is purified by the same manner as in the first method to give the desired compound (I).
- the comound (I) is prepared by reacting a compound having the formula (VIII): wherein R 1 is as defined above, and a compound having the formula (IX): wherein R 2 is as defined above, in an inert solvent in the presence of a basic compound.
- the compound (IX) is employed in an amount of not less than 1.0 mole, generally 1.05 to 1.3 moles, per 1 mole of the compound (VIII).
- the basic compound are, for instance, a tertiary amine such as pyridine or triethylamine, sodium carbonate, and the like.
- the inert solvent are, for instance, ethyl acetate, methylene chloride, chloroform, toluene, benzene, and the like. It is preferred to add slowly the compound (IX) with cooling while maintaining a temperature in the range of from room temperature to 40°C because of the exothermic reaction.
- the above reaction also can be carried out by using an acid anhydride such as acetic anhydride or butyric anhydride instead of the compound (IX) such as acetyl chloride or butyryl chloride.
- an acid anhydride such as acetic anhydride or butyric anhydride
- the reaction mixture is purified in the same manner as in the first method to give the desired compound (I).
- Example 1 The procedure of Example 1 was repeated except that reaction conditions such as a kind of reactant and solvent, reaction time and reaction temperature were changed as shown in Table 1. The obtained results are shown in Table 1.
- Example 13 The procedure of Example 13 was repeated except that reaction conditions such as a kind of reactant and solvent, reaction time and reaction temperature were changed as shown in Table 2. The results are shown in Table 2. Each compound obtained was analyzed by gas chromatography and thin layer chromatography.
- Example 26 The procedure of Example 26 was repeated except that reaction conditions such as a kind of reactant and solvent, reaction time and reaction temperature were changed as shown in Table 3. The results are shown ih Table 3.
- each compound obtained was subjected to analysis by gas chromatography and thin layer chromatography. As a result, each retention time and R f value were consistent with those of the compounds obtained in Examples 1 to 5, 7 and 10 to 12, respectively.
- the obtained syrup was analyzed by gas chromatography and thin layer chromatography. As a result, the retention time and the Rf value were consistent with those of the compound obtained in Example 1.
- Example 36 The procedure of Example 36 was repeated except that succinic anhydride was used instead of acetic anhydride. The results are shown in Table 4.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58316/83 | 1983-04-02 | ||
| JP5831683A JPS59184169A (ja) | 1983-04-02 | 1983-04-02 | ５−アシロキシメチル−２−オキサゾリジノン誘導体及びその製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0123719A2 true EP0123719A2 (de) | 1984-11-07 |
| EP0123719A3 EP0123719A3 (en) | 1985-09-18 |
| EP0123719B1 EP0123719B1 (de) | 1989-12-13 |
Family
ID=13080853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP83107961A Expired EP0123719B1 (de) | 1983-04-02 | 1983-08-11 | Verfahren zur Herstellung von 5-Acyloxymethyl-oxazolidin-2-on-derivaten. |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0123719B1 (de) |
| JP (1) | JPS59184169A (de) |
| DE (1) | DE3380957D1 (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0209001A1 (de) * | 1985-07-18 | 1987-01-21 | Heinz-Hermann Dr. Bokel | 1-Oxa-2-oxo-3-R-3-aza-5-Z-cyclopentanderivate |
| US4925862A (en) * | 1987-07-20 | 1990-05-15 | Roussel Uclaf | Novel pyrethrinoids |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2121442A1 (en) * | 1971-01-14 | 1972-08-25 | Delalande Sa | 5-hydroxymethyl-3-phenyl-oxazolidone-2-esters - - antidepressants, anticonvulsants, tranquillisers and analgesics |
| EP0101076A2 (de) * | 1982-08-13 | 1984-02-22 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Verfahren zur Herstellung von optisch aktiven Oxazolidinon-Derivaten |
-
1983
- 1983-04-02 JP JP5831683A patent/JPS59184169A/ja active Granted
- 1983-08-11 DE DE8383107961T patent/DE3380957D1/de not_active Expired - Fee Related
- 1983-08-11 EP EP83107961A patent/EP0123719B1/de not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2121442A1 (en) * | 1971-01-14 | 1972-08-25 | Delalande Sa | 5-hydroxymethyl-3-phenyl-oxazolidone-2-esters - - antidepressants, anticonvulsants, tranquillisers and analgesics |
| EP0101076A2 (de) * | 1982-08-13 | 1984-02-22 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Verfahren zur Herstellung von optisch aktiven Oxazolidinon-Derivaten |
Non-Patent Citations (1)
| Title |
|---|
| Oxozoles, I. J. Turchi, p. 662 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0209001A1 (de) * | 1985-07-18 | 1987-01-21 | Heinz-Hermann Dr. Bokel | 1-Oxa-2-oxo-3-R-3-aza-5-Z-cyclopentanderivate |
| US4925862A (en) * | 1987-07-20 | 1990-05-15 | Roussel Uclaf | Novel pyrethrinoids |
| US5008281A (en) * | 1987-07-20 | 1991-04-16 | Roussel Uclaf | Novel pyrethrinoids |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH037672B2 (de) | 1991-02-04 |
| DE3380957D1 (de) | 1990-01-18 |
| EP0123719A3 (en) | 1985-09-18 |
| EP0123719B1 (de) | 1989-12-13 |
| JPS59184169A (ja) | 1984-10-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4152326A (en) | Cyclic sulphonyloxyimides | |
| US4910306A (en) | Preparation of substituted 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonanilides | |
| JP3180192B2 (ja) | ジチオカルバミン酸の塩類、その製造方法及び該ジチオカルバミン酸の塩類を使用するイソチオシアネート類の製造方法 | |
| EP0123719A2 (de) | Verfahren zur Herstellung von 5-Acyloxymethyl-oxazolidin-2-on-derivaten. | |
| EP0135304B1 (de) | Verfahren zur Herstellung von substituierten Benzamiden | |
| EP1471071A1 (de) | Verfahren zur Herstellung von 5'-Acyloxynukleosidderivat | |
| SU507239A3 (ru) | Способ получени 2-гидразинобензотиазолов | |
| KR20010005943A (ko) | 0-(3-아미노-2-히드록시-프로필)-히드록심산할라이드의 제조방법 | |
| US4731479A (en) | N-sulfamyl-3-halopropionamidines | |
| JPS6360969A (ja) | イミダゾ−ル誘導体の製造方法 | |
| US4814500A (en) | Cyanoguanidine derivative and process for preparation thereof | |
| US4353836A (en) | 4-(2,5-Dihydroxyphen-1-yl)-crotonic acid and its derivatives, and the preparation of these compounds | |
| EP0034421B1 (de) | N-Phenyl-N'-cyano-O-phenylisoharnstoffe und Verfahren zu deren Herstellung | |
| KR0142140B1 (ko) | 2-벤조일-3-아미노아크릴레이트 유도체의 제조방법 | |
| KR800000383B1 (ko) | 3-이속사졸릴 요소 유도체의 제조 방법 | |
| KR800000380B1 (ko) | 3-이속사졸릴 요소 유도체의 제조방법 | |
| JP3066594B2 (ja) | アニリン誘導体及びその製造法 | |
| KR800000431B1 (ko) | 3-이속사졸릴 요소 유도체의 제조방법 | |
| KR800000384B1 (ko) | 3-이속사졸릴 요소 유도체의 제조방법 | |
| JP3850930B2 (ja) | ５−シアノ−２−スルホニルピリジンおよびその製造方法 | |
| KR860000850B1 (ko) | 인돌초산 유도체의 제조방법 | |
| US5003096A (en) | Preparation of substituted 1,2,4-triazolo[1,4-a]pyrimidine-2-sulfonanilides | |
| US4363926A (en) | Preparation of novel 1-hydroxycyclopropanecarboxylic acid intermediates | |
| US4892956A (en) | 5-cyano-4,5-dihydro-3,4-dicarboxypyrazole derivatives | |
| US4459415A (en) | Process for the preparation of 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxyacetic acid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| AK | Designated contracting states |
Designated state(s): BE CH DE FR GB IT LI NL SE |
|
| PUAL | Search report despatched |
Free format text: ORIGINAL CODE: 0009013 |
|
| AK | Designated contracting states |
Designated state(s): BE CH DE FR GB IT LI NL SE |
|
| 17P | Request for examination filed |
Effective date: 19860308 |
|
| 17Q | First examination report despatched |
Effective date: 19871207 |
|
| GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
| AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): BE CH DE FR GB IT LI NL SE |
|
| REF | Corresponds to: |
Ref document number: 3380957 Country of ref document: DE Date of ref document: 19900118 |
|
| ET | Fr: translation filed | ||
| ITF | It: translation for a ep patent filed | ||
| PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
| 26N | No opposition filed | ||
| ITTA | It: last paid annual fee | ||
| EAL | Se: european patent in force in sweden |
Ref document number: 83107961.1 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: SE Payment date: 19970818 Year of fee payment: 15 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: GB Payment date: 19980803 Year of fee payment: 16 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19980812 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 19980814 Year of fee payment: 16 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DE Payment date: 19980817 Year of fee payment: 16 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: CH Payment date: 19980824 Year of fee payment: 16 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: NL Payment date: 19980827 Year of fee payment: 16 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: BE Payment date: 19981016 Year of fee payment: 16 |
|
| EUG | Se: european patent has lapsed |
Ref document number: 83107961.1 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GB Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19990811 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LI Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19990831 Ref country code: CH Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19990831 Ref country code: BE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19990831 |
|
| BERE | Be: lapsed |
Owner name: KANEGAFUCHI KAGAKU KOGYO K.K. Effective date: 19990831 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20000301 |
|
| GBPC | Gb: european patent ceased through non-payment of renewal fee |
Effective date: 19990811 |
|
| REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FR Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20000428 |
|
| NLV4 | Nl: lapsed or anulled due to non-payment of the annual fee |
Effective date: 20000301 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20000601 |
|
| REG | Reference to a national code |
Ref country code: FR Ref legal event code: ST |